Live the Highland Lake Dream - 431 W. Wakefield Blvd, Winchester, CT Summer is just around the corner - and in Winsted, resort living never ends. Recently named one of the most desirable towns to live in, with the breathtaking Highland Lake at its heart, Winchester offers the perfect blend of beauty and lifestyle. This waterfront estate at 431 W. Wakefield Blvd isn't just a home - it's your gateway to the ultimate lake life. Wake each morning to panoramic water views, and step outside to a world of four-season recreation. In summer, enjoy boating, jet skiing, swimming, and fishing right from your private dock, or simply relax by the shoreline. When winter arrives, the lake transforms into your own frozen wonderland for ice fishing, skating, and fireside gatherings. Inside, luxury awaits. The main home features gourmet finishes, a chef's kitchen, and custom craftsmanship throughout. A charming guest bungalow offers privacy for family, friends, or guests. Zoned for a bed and breakfast, and featuring an extra subdividable lot, the property offers immense potential - whether as a private retreat, an upscale B&B, or an investment in future development. Set on 425 feet of pristine water frontage, this estate captures the essence of Highland Lake living - natural beauty, year-round recreation, and endless opportunity.
Under contract
$1,850,000
431 West Wakefield Boulevard, Winchester, CT 06098
9beds
7,000sqft
Single Family Residence
Built in 2002
3 Acres Lot
$-- Zestimate®
$264/sqft
$-- HOA
What's special
Waterfront estateCharming guest bungalowPrivate dockPanoramic water viewsRelax by the shorelineCustom craftsmanship throughoutGourmet finishes
- 117 days
- 171
- 4
Zillow last checked:
Listing updated:
Listed by:
Lisa A. Ogren (860)416-2085,
Berkshire Hathaway NE Prop. 860-677-7321
Source: Smart MLS,MLS#: 24159989
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 9
- Bathrooms: 6
- Full bathrooms: 5
- 1/2 bathrooms: 1
Rooms
- Room types: Bonus Room
Primary bedroom
- Features: Bedroom Suite, Ceiling Fan(s), Full Bath, Walk-In Closet(s)
- Level: Main
- Area: 336 Square Feet
- Dimensions: 21 x 16
Bedroom
- Features: Ceiling Fan(s)
- Level: Upper
- Area: 345 Square Feet
- Dimensions: 23 x 15
Bedroom
- Features: Ceiling Fan(s)
- Level: Upper
- Area: 299 Square Feet
- Dimensions: 23 x 13
Bedroom
- Features: Ceiling Fan(s)
- Level: Upper
- Area: 276 Square Feet
- Dimensions: 23 x 12
Bedroom
- Features: Ceiling Fan(s)
- Level: Upper
- Area: 276 Square Feet
- Dimensions: 23 x 12
Bedroom
- Level: Upper
Bedroom
- Level: Upper
- Area: 182 Square Feet
- Dimensions: 13 x 14
Bedroom
- Level: Upper
- Area: 264 Square Feet
- Dimensions: 24 x 11
Bedroom
- Level: Upper
- Area: 288 Square Feet
- Dimensions: 24 x 12
Dining room
- Features: Remodeled, Bay/Bow Window, Built-in Features, Patio/Terrace
- Level: Main
- Area: 208 Square Feet
- Dimensions: 16 x 13
Family room
- Features: Fireplace
- Level: Lower
Kitchen
- Features: Bay/Bow Window, Eating Space
- Level: Main
- Area: 360 Square Feet
- Dimensions: 24 x 15
Library
- Level: Main
- Area: 208 Square Feet
- Dimensions: 16 x 13
Living room
- Features: Fireplace
- Level: Main
- Area: 1518 Square Feet
- Dimensions: 33 x 46
Other
- Level: Upper
- Area: 253 Square Feet
- Dimensions: 23 x 11
Heating
- Baseboard, Oil
Cooling
- Attic Fan, Window Unit(s)
Appliances
- Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Disposal, Dryer, Water Heater
- Laundry: Lower Level
Features
- Central Vacuum
- Doors: French Doors
- Basement: Full,Heated,Garage Access,Interior Entry,Liveable Space
- Attic: Heated,Finished,Floored
- Number of fireplaces: 4
Interior area
- Total structure area: 7,000
- Total interior livable area: 7,000 sqft
- Finished area above ground: 5,530
- Finished area below ground: 1,470
Video & virtual tour
Property
Parking
- Total spaces: 9
- Parking features: Barn, Attached, Off Street, Driveway, Garage Door Opener, Private, Paved
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Features
- Patio & porch: Deck, Covered
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Waterfront, Lake, Beach, Dock or Mooring, Water Community
Lot
- Size: 3 Acres
- Features: Additional Land Avail., Few Trees, Level, Landscaped, Rolling Slope
Details
- Additional structures: Cabana
- Parcel number: 924886
- Zoning: HLD
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape Cod,Colonial
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 2002
Utilities & green energy
- Sewer: Public Sewer
- Water: Well
- Utilities for property: Cable Available
Community & HOA
Community
- Features: Public Rec Facilities
- Security: Security System
HOA
- Has HOA: No
Location
- Region: Winsted
Financial & listing details
- Price per square foot: $264/sqft
- Tax assessed value: $832,720
- Annual tax amount: $24,982
- Date on market: 5/7/2026
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 8/3/2026 | Pending sale | $1,850,000$264/sqft |
Source:  Smart MLS #24159989 Report a problem | ||
| 5/7/2026 | Listed for sale | $1,850,000$264/sqft |
Source: Smart MLS #24159989 Report a problem | ||
| 4/20/2026 | Listing removed | $1,850,000$264/sqft |
Source:  Berkshire Hathaway HomeServices New England Properties #24159989 Report a problem | ||
| 3/25/2026 | Listed for sale | $1,850,000-15.9%$264/sqft |
Source: Smart MLS #24159989 Report a problem | ||
| 2/1/2026 | Listing removed | $2,199,000$314/sqft |
Source: Smart MLS #24042374 Report a problem | ||
| 7/9/2025 | Price change | $2,199,000-15.4%$314/sqft |
Source: Smart MLS #24042374 Report a problem | ||
| 3/26/2025 | Price change | $2,600,000-7.1%$371/sqft |
Source: Smart MLS #24042374 Report a problem | ||
| 9/4/2024 | Listed for sale | $2,800,000+154.5%$400/sqft |
Source: Smart MLS #24042374 Report a problem | ||
| 3/20/2014 | Listing removed | $1,100,000$157/sqft |
Source: Keller Williams Realty #G635346 Report a problem | ||
| 5/14/2013 | Listed for sale | $1,100,000$157/sqft |
Source: Keller Williams Realty #G635346 Report a problem | ||
| 5/11/2013 | Pending sale | $1,100,000$157/sqft |
Source: Keller Williams Realty #G635346 Report a problem | ||
| 1/6/2013 | Price change | $1,100,000-18.5%$157/sqft |
Source: Keller Williams Realty #G635346 Report a problem | ||
| 10/18/2012 | Price change | $1,350,000+3.8%$193/sqft |
Source: Keller Williams Realty #G635346 Report a problem | ||
| 8/4/2012 | Listed for sale | $1,300,000-27.8%$186/sqft |
Source: Borla & Associates LLC Real Estate #L140243 Report a problem | ||
| 4/6/2012 | Listing removed | $1,800,000$257/sqft |
Source: Borla & Associates LLC Real Estate #L140243 Report a problem | ||
| 10/5/2011 | Listed for sale | $1,800,000+800%$257/sqft |
Source: Borla & Associates LLC Real Estate #L140243 Report a problem | ||
| 10/30/1998 | Sold | $200,000$29/sqft |
Source: Agent Provided Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $24,184 +10.5% | $829,080 |
| 2024 | $21,879 | $829,080 |
| 2023 | $21,879 +18.6% | $829,080 +50.7% |
| 2022 | $18,447 | $549,990 |
| 2021 | $18,447 | $549,990 |
| 2020 | $18,447 | $549,990 |
| 2019 | $18,447 | $549,990 |
| 2018 | $18,447 +2.3% | $549,990 +2.3% |
| 2017 | $18,029 +0.4% | $537,530 +0.4% |
| 2016 | $17,951 +2.6% | $535,220 |
| 2015 | $17,502 +2.5% | $535,220 |
| 2014 | $17,079 +2.3% | $535,220 |
| 2013 | $16,699 +2.5% | $535,220 -16.5% |
| 2012 | $16,295 | $640,780 |
| 2011 | $16,295 | $640,780 |
| 2010 | $16,295 +3.1% | $640,780 |
| 2009 | $15,808 | $640,780 |
| 2008 | $15,808 +35.8% | $640,780 +88.6% |
| 2007 | $11,642 +3.6% | $339,710 +0.8% |
| 2006 | $11,235 +16% | $336,980 +14.8% |
| 2005 | $9,685 +151.3% | $293,650 +129.5% |
| 2003 | $3,854 +20.4% | $127,960 +10.2% |
| 1995 | $3,201 | $116,130 |
Find assessor info on the county website
Monthly payment
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